 | This article includes a list of general references, but it lacks sufficient corresponding inline citations. (August 2013) |
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| Names | |
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| IUPAC name
2H-Oxadiazol-5-one
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| Other names
1,2,3-Oxadiazol-5(2H)-one
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| Properties | |
| C2H2N2O2 | |
| Molar mass | 86.050 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sydnones are mesoionic heterocyclic chemical compounds possessing a 1,2,3-oxadiazole core with a keto group in the 5 position.[1][2][3] Like other mesoionic compounds they are di-polar, possessing both positive and negative charges which are delocalized across the ring. Recent computational studies have indicated that sydnones and other similar mesoionic compounds are nonaromatic, "though well-stabilized in two separate regions by electron and charge delocalization."[4] Sydnones are heterocyclic compounds named after the city of Sydney, Australia.
A sydnone imine in which the keto group of sydnone (=O) has been replaced with an imino (=NH) group can be found as a substructure in the stimulant drugs feprosidnine and mesocarb.
- ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "sydnones". doi:10.1351/goldbook.S05990
- ^ Stewart, F. H. C. (1 April 1964). "The Chemistry of the Sydnones". Chemical Reviews. 64 (2): 129–147. doi:10.1021/cr60228a004.
- ^ Browne, Duncan L.; Harrity, Joseph P.A. (January 2010). "Recent developments in the chemistry of sydnones". Tetrahedron. 66 (3): 553–568. doi:10.1016/j.tet.2009.10.085.
- ^ Simas, Alfredo (1998). "Are mesoionic compounds aromatic?". Canadian Journal of Chemistry. 76 (6): 869–872. doi:10.1139/v98-065.